April 26, 2023

Re:     Offer of Employment

Dear Blake:

I am pleased to offer you a position with DocuSign, Inc. (the “Company” or “DocuSign”) as Executive Vice President and Chief Financial Officer, reporting to me, with an expected commencement date of June 19, 2023 or such earlier date as you and I may mutually agree (“Start Date”). Please note that if your Start Date occurs prior to the date on which DocuSign files its quarterly report on Form 10-Q for the quarter ended April 30, 2023, your position as Chief Financial Officer will commence on the first business day following such date. Your primary work location will be our office in Seattle, WA, subject to regular travel to the Company’s other offices from time to time when reasonably necessary or appropriate to perform your duties. You will receive an initial annual salary of $500,000, less applicable taxes and deductions, which will be paid biweekly in accordance with the Company’s normal payroll procedures. In addition, you will be eligible for a target bonus equal to 100% of your then-current annual salary, subject to the terms and conditions of the Company Incentive Plan (“CIP”) in effect for each applicable fiscal year. The CIP document contains important information including eligibility, pro-ration for employees on a leave of absence or hired mid-year, and the measures used to track Company’s achievement of targets for the plan year as established by the Board or a committee thereof.

Sign-On Bonus. The Company will pay you a one-time signing bonus of $1,000,000 (the “Sign-On Bonus”), to be paid out in your first payroll following your Start Date. The Sign-On Bonus will be subject to withholding requirements and authorized deductions. The payment of the Sign-On Bonus is an advance and will not be fully earned unless you remain employed by DocuSign for one full year from your Start Date. If you resign without Good Reason or are terminated by DocuSign for Cause before the one-year anniversary of your Start Date you agree to repay the full amount of the Sign-On Bonus advance at the time of your departure (less 8.33% for each full month of work completed after your Start Date). In the event of a Qualifying Termination prior to the one-year anniversary of your Start Date, DocuSign will waive any right to recoup any portion of the Sign-On Bonus. As a condition of receiving the Sign-On Bonus advance, you agree and authorize the Company to deduct any unearned portion of the advance from your final wages, to the extent permitted by applicable laws. If you fail to repay the Sign-On Bonus advance within fourteen days of your departure, interest will accrue on the amount owed at the rate of 1.5% per month. In addition to paying interest, should any dispute arise concerning your obligation to repay the Sign-On Bonus and an arbitration or other legal proceeding results, the prevailing party in any such dispute shall be entitled to recover its or his reasonable attorneys’ fees and costs incurred to the extent they concern the Sign-On Bonus, its repayment, and/or your obligation to repay it.

For purposes of this offer letter, “Cause,” “Good Reason” and “Qualifying Termination” have the same meanings as those terms are used in the Company’s Executive Severance and Change in Control Agreement, attached hereto.

Equity Awards. As soon as practicable after your Start Date, you shall receive the following awards of restricted stock units (“RSUs”) representing the right to acquire shares of Common Stock of DocuSign, Inc.:

•A new hire grant of time-vesting RSUs with a target value of $20 million (the “New Hire Grant”);

•An additional grant of time-vesting RSUs with a target value of $7.5 million (the “First Additional Grant”); and

•An additional grant of time-vesting RSUs with a target value of $5 million (the “Second Additional Grant”).

The number of RSUs you receive will generally be determined by dividing the applicable target value by the average closing stock price over a period of 60 trading days immediately prior to the Vesting Commencement Date. The Vesting Commencement Date will be the 10th day of the calendar month occurring concurrently with or after your Start Date. Such RSUs will be subject to the terms and conditions of: (a) the Company’s equity incentive plan in effect at the time of grant (the “Plan”), (b) an RSU Agreement in the form approved by the Board or a committee of the Board, and (c) applicable law. The RSUs will be subject to service-based requirements as set forth in the RSU Agreement. For a general summary of the vesting terms, please see Attachment A hereto.

Severance & Change in Control Agreement. You and the Company will enter into the Executive Severance and Change in Control Agreement in the form attached hereto.

Additional Benefits. As a Company employee, you will also be eligible to receive certain employee benefits including PTO, healthcare, dental coverage, and a 401(k) plan on terms no less favorable than any other U.S. based executive officer. You should note that the Company may modify salaries and benefits from time to time as it deems necessary. You should be aware that your employment with the Company is for no specified period and constitutes at-will employment. As a result, you are free to resign at any time, for any reason or for no reason.

Similarly, the Company is free to conclude its employment relationship with you at any time, with or without cause, and with or without notice.

For purposes of federal immigration law, you will be required to provide to the Company documentary evidence of your identity and eligibility for employment in the United States. Such documentation must be provided to us within three (3) business days of your date of hire, or our employment relationship with you may be terminated. If you require work authorization to lawfully work in the U.S., this must be obtained prior to your State Date and your Start Date is subject to change if proof of such authorization is not obtained by the Company by Monday of the week prior to your Start Date.

You will be expected to devote your full working time and attention to the business of the Company, and you will not render services to any other business without the prior approval of the Board. Notwithstanding the foregoing, you may manage personal investments, participate in civic, charitable, and academic activities (if in a limited, non-leadership capacity unless a larger role is approved by the Board), and, subject to prior approval by the Board, serve on the board of directors (and any committees) and/or as an advisor of other for-profit companies, provided that such activities do not at the time the activity or activities commence or thereafter (a) create an actual or potential business or fiduciary conflict of interest or (b) individually or in the aggregate, interfere materially with the performance of your duties to the Company.

As a Company employee, you will be required to abide by Company rules and regulations. You will be specifically required to sign an acknowledgement that you have read and understand the company rules of conduct which are included in the employee handbook which you will receive on your first day of employment.

You will be required to sign and comply with an At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement which requires, among other provisions, the assignment of patent rights to any invention made during your employment at the Company and non-disclosure of proprietary information. Such Agreement also provides that in the event of any dispute or claim relating to or arising out of our working relationship, you and the Company agree that all such disputes shall be resolved by binding arbitration.

Expenses. The Company will, in accordance with applicable Company policies and guidelines, reimburse you for all reasonable and necessary expenses you incur in connection with the performance of services on behalf of the Company during your employment with the Company, on terms no less favorable than for any other U.S. based executive officer of the Company. In addition, subject to and promptly following the Start Date the Company will reimburse your fair, reasonable and documented expenses for legal or other advisors incurred in the review and finalization of this Agreement and related documentation (not to exceed $4,000). Subject to the preceding, the reimbursement for all such expenses shall be paid pursuant to the Company’s policies and practices, following your submission of proper documentation for such expenses.

Indemnification. You and the Company will enter into an indemnification agreement on substantially the same terms applicable to the Company’s other officers and directors. In addition, you will be named as an insured on the director and officer liability insurance policy currently maintained by the Company, or as may be maintained by the Company from time to time, on terms no less favorable than for any other U.S. based executive officer of the Company.

Compensation Recoupment. Certain incentive-based compensation payable to you shall be subject to recoupment pursuant to the Company’s current compensation clawback or recoupment policy (if any) and any additional compensation clawback or recoupment policy or amendments to the current policy adopted by the Board or as required by law that applies on substantially the same terms to all other U.S. based executive officers of the Company (except as required by statute or regulation without regard to the terms of the policy). No recovery of compensation under such a clawback or recoupment policy will be an event giving rise to a right to resign for “Good Reason” or constitute a termination without “Cause” under this agreement, provided that such recovery is consistent with such policy and such policy is consistent with this paragraph.

To indicate your acceptance of the Company’s offer, please sign and date this letter in the space provided below on or before May 5, 2023. This letter (including any documents referenced herein), along with the agreement relating to proprietary rights between you and the Company, set forth the terms of your employment with the Company and supersede any prior representations or agreements, whether written or oral. This letter may not be modified or amended except by a written agreement, signed by an officer of the Company and by you.

We look forward to working with you at DocuSign, Inc.

Sincerely,

DocuSign, Inc.

/s/ Allan Thygesen                    

/s/ Blake Grayson        

As provided in more detail in the applicable RSU Agreement, your RSUs will become “Vested RSUs” subject to the satisfaction of the following service-based requirements:

•New Hire Grant, $20m target value: 1/16th of the total number of RSUs awarded will vest on each of the 16 quarterly anniversaries of the Vesting Commencement Date, subject to you remaining in Continuous Service (as defined in the Plan) with the Company on each such date.

•First Additional Grant, $7.5m target value: 100% of the total number of RSUs awarded will vest on the 12-month anniversary of the Vesting Commencement Date, subject to you remaining in Continuous Service with the Company on such date.

•Second Additional Grant, $5m target value: 25% of the total number of RSUs awarded will vest on the 15-month anniversary of the Vesting Commencement Date, and thereafter 25% of the total number of RSUs awarded will vest in a series of 3 successive equal quarterly installments following such first vesting date subject to you remaining in Continuous Service with the Company on each such date.

Vested RSUs will generally be delivered to you (“settled”) on a quarterly basis (March, June, September and December) following the date on which the RSUs become vested.

The RSUs will be subject to the terms and conditions of the Plan and the applicable RSU Agreement.

You will be entitled to receive such accelerated vesting of your outstanding time-vesting equity awards consistent with the terms and conditions of the Company’s Death or Terminal Condition Policy, as may be amended from time to time, and your Executive Severance and Change in Control Agreement.

DOCUSIGN, INC.
EXECUTIVE SEVERANCE AND CHANGE IN CONTROL AGREEMENT

This Executive Severance and Change in Control Agreement (the “Agreement”) by and between Blake Grayson (“Executive”) and DocuSign, Inc., a Delaware corporation (the “Company”) is effective as of the date set forth on the signature page hereto (the “Agreement Date”).

A.    The Company’s Board of Directors (the “Board”) or the Compensation Committee of the Board (the “Committee”) believes it is in the best interests of the Company and its stockholders to hire Executive and to provide Executive with certain protections in the event of Executive’s termination of employment or a Change in Control of the Company under certain circumstances.

B.    To accomplish the foregoing objectives, the Committee has directed the Company, upon execution of this Agreement by Executive, to agree to the terms provided in this Agreement. Capitalized terms not defined below shall have the meanings set forth in Exhibit A or Exhibit B, as applicable.

The parties hereto agree as follows:

1.At-Will Employment. Nothing in this Agreement alters the at-will nature of Executive’s employment. Executive and the Company remain free to terminate the employment relationship at any time, for any reason, with or without notice. If Executive’s employment is terminated by Executive or the Company for any reason, Executive agrees to promptly resign from all positions Executive may hold with the Company (including as a member of the Board, if applicable) and any of its subsidiaries or affiliated entities at such time (unless otherwise requested by the Board or Committee).

2.Benefits Upon Qualifying Termination Outside the Change in Control Period. Upon Executive’s Qualifying Termination outside a Change in Control Period, and subject to the conditions in Section 4, the Company will provide Executive with the following severance benefits:

a.Severance Pay. The Company will pay Executive a lump sum cash payment, less all applicable withholdings and deductions, in an amount equal to:

i.12 months of Executive’s then-current base salary (ignoring any decrease in base salary that forms the basis for Good Reason); and

ii.100% of Executive’s target annual bonus for the performance year in which the Qualifying Termination occurs.

b.Continued Health Insurance Coverage. Provided Executive timely elects COBRA continuation coverage, the Company will pay the COBRA premiums to continue and maintain health care coverage for Executive and any dependents who are covered at the time of the Executive’s termination of employment under the Company’s group health plans. The Company will make such payments until the earliest of: (i) 12 months following the Qualifying Termination date; (ii) the date when Executive becomes eligible for substantially equivalent health insurance coverage in connection with new employment or self-employment; or (iii) the date Executive ceases to be eligible for COBRA continuation coverage for any reason. Notwithstanding the foregoing, if the Company determines in its sole discretion that it cannot pay the COBRA premiums without potentially incurring financial costs or penalties under applicable law, the Company may pay Executive a taxable cash payment equal to the amount that the Company would have otherwise paid for COBRA premiums (based on the premium for the first month of coverage), which payment will be made regardless of whether Executive or Executive’s eligible dependents elect COBRA continuation coverage and will be paid in monthly installments on the same schedule and over the same time period that the COBRA premiums would otherwise have been paid on behalf of Executive.

c.Equity Vesting Acceleration. The vesting of each of Executive’s then outstanding equity compensation awards granted under any of the Company’s equity incentive plans (“Company Equity Awards”) (other than Performance Awards (as defined below)) will accelerate as to the number of shares subject to each such award that would have become vested, in the ordinary course, within the first 12 months following Executive’s termination date, effective on Executive’s date of termination. With respect to awards that would otherwise vest only upon satisfaction of performance criteria (“Performance Awards”), the vesting of such awards will accelerate as set forth in the terms of the applicable performance-based equity award agreement.

Subject to the payment timing rules contained in Exhibit B, any severance payments and benefits under this Section 2 will be paid on the later of (x) 10 business days after the effective date of the Release and (y) the date of Executive’s Qualifying Termination.

3.Qualifying Termination During the Change in Control Period. Upon Executive’s Qualifying Termination during the Change in Control Period, and subject to the conditions in Section 5, the Company will provide Executive with the following severance benefits:

a.Severance Pay. The Company will pay Executive a lump sum cash payment, less all applicable withholdings and deductions, in an amount equal to:

i.12 months of Executive’s then-current base salary (ignoring any decrease in base salary that forms the basis for Good Reason); and

ii.No target annual bonus for the performance year in which the Qualifying Termination occurs (this means no pro rata or partial annual bonus payment will be owed).

b.Continued Health Insurance Coverage. Provided Executive timely elects COBRA continuation coverage, the Company will pay the COBRA premiums to continue and maintain health care coverage for Executive and any dependents who are covered at the time of the Executive’s termination of employment under the Company’s group health plans. The Company will make such payments until the earliest of: (i) 12 months following the Qualifying Termination date; (ii) the date when Executive becomes eligible for substantially equivalent health insurance coverage in connection with new employment or self-employment; or (iii) the date Executive ceases to be eligible for COBRA continuation coverage for any reason. Notwithstanding the foregoing, if the Company determines in its sole discretion that it cannot pay the COBRA premiums without potentially incurring financial costs or penalties under applicable law, the Company may pay Executive a taxable cash payment equal to the amount that the Company would have otherwise paid for COBRA premiums (based on the premium for the first month of coverage), which payment will be made regardless of whether Executive or Executive’s eligible dependents elect COBRA continuation coverage and will be paid in monthly installments on the same schedule and over the same time period that the COBRA premiums would otherwise have been paid on behalf of Executive.

c.Equity Vesting Acceleration. The vesting of each of Executive’s Company Equity Awards (other than Performance Awards) will accelerate in full. The vesting of Performance Awards will accelerate as set forth in the terms of the applicable performance-based equity award agreement. In order to accommodate this potential accelerated vesting, if Executive experiences a Qualifying Termination within 90 days prior to a Change in Control, any then-unvested compensatory equity awards will not terminate with respect to shares that have not vested as of Executive’s termination date until 6 months and one day after Executive’s termination date.

Subject to the payment timing rules contained in Exhibit B, any severance payments and benefits under this Section 3 will be paid on the latest of (x) 10 business days after the effective date of the Release, (y) the date of Executive’s Qualifying Termination, and (z) the date of the Change in Control.

4.Limitations and Conditions on Termination Benefits

a.Release Prior to Payment of Benefits. In order to be eligible to receive any benefits under Sections 2 or 3, Executive must (i) execute and return a general waiver and release, in a form provided by the Company and reasonably acceptable to Executive, of all claims and causes of action against the Company (a “Release”), to the Company within the applicable time period set forth therein and (ii) not revoke the Release within the revocation period (if any) set forth therein; provided, however, that in no event may the applicable time period or revocation period extend beyond sixty (60) days following Executive’s termination date.

b.Income and Employment Taxes. Executives agrees that Executive will be responsible for any applicable taxes of any nature (including any penalties or interest that may apply to such taxes) that the Company reasonably determines apply to any payment made hereunder, that Executive’s receipt of any benefit hereunder is conditioned on Executive’s satisfaction of any applicable withholding or similar obligations that apply to such benefit, and that any cash payment owed hereunder will be reduced to satisfy any such withholding or similar obligations that may apply.

c.Related Matters. Executive further acknowledges and agrees that as a condition to receipt of any severance benefits, Executive must (i) comply with Executive’s obligations under Executive’s At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement; and (ii) resign from all officer and director positions with the Company and/or any affiliate (unless otherwise requested by the Board or Committee).

d.Section 409A and Section 280G. Executive and the Company understand that payments under this Agreement may be subject to Sections 409A and 280G of the Code, and the parties agree to abide by the Section 409A and Section 280G provisions contained in Exhibit B to this Agreement.

e.Clawback/Recoupment. Certain incentive-based compensation payable to Executive shall be subject to recoupment pursuant to the Company’s current compensation clawback or recoupment policy (if any) and any additional compensation clawback or recoupment policy or amendments to the current policy adopted by the Board or as required by law that applies on substantially the same terms to all other U.S. based executive officers of the Company (except as required by statute or regulation without regard to the terms of the policy). No recovery of compensation under such a clawback or recoupment policy will be an event giving rise to a right to resign for “Good Reason” or constitute a termination without “Cause” under this agreement, provided that such recovery is consistent with such policy and such policy is consistent with this paragraph.

5.Miscellaneous Provisions.

a.Interaction with Other Benefits. In the event that Executive would be entitled to a greater level of payments or benefits under the terms and conditions of an individual equity compensation award, offer letter or other employment-related agreement, or a severance plan or policy provided by the Company or its successor, but for the existence of this Agreement, Executive shall be entitled to receive the greater of the payments and benefits provided for hereunder or the benefits under such other agreement, plan or policy subject to the applicable terms and conditions thereof.

b.Complete Agreement. Notwithstanding anything to the contrary herein, this Agreement supersedes any agreement (or portion thereof) concerning similar subject matter dated prior to the Agreement Date, and by execution of this Agreement both parties agree that any such predecessor agreement (or portion thereof) shall be deemed null and void; provided that, for clarification purposes, this Agreement shall not affect any agreement between the Company and Executive regarding intellectual property matters, non-solicitation or non- competition restrictions or confidential information. The parties further agree that this Agreement does not supersede the provisions of Executive’s offer letter or employment agreement with the Company which do not address termination or severance benefits or Executive’s At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement.

c.Waiver. No provision of this Agreement may be waived unless the waiver is agreed to in writing and signed by Executive and by an authorized officer of the Company. No waiver by either party of any breach of, or of compliance with, any condition or provision of this Agreement shall be considered a waiver at another time.

d.Successors and Assigns. This Agreement is personal to Executive and will not be assignable by Executive otherwise than by will or the laws of descent and distribution. This Agreement will inure to the benefit of and be binding upon the Company and its successors and assigns. From and after a Change in Control, the term “Company” when used in this Agreement will also be read to include any entity that actually employs Executive, if different from the Company.

e.Choice of Law. The validity, interpretation, construction and performance of this Agreement shall be governed by the laws of the State of California without reference to conflict of laws provisions, and the parties hereto submit to the exclusive jurisdiction of the state and federal courts of the State of California.

f.Severability. The invalidity or unenforceability of any provision or provisions of this Agreement shall not affect the validity or enforceability of any other provision hereof, which shall remain in full force and effect.

g.Notice. Notices and all other communications contemplated by this Agreement will be in writing and will be deemed to have been duly given when personally delivered or when mailed by U.S. registered or certified mail, return receipt requested and postage prepaid. Mailed notices to Executive shall be addressed to Executive at the home address which Executive most recently communicated to the Company in writing. In the case of the Company, mailed notices shall be addressed to its corporate headquarters, and all notices shall be directed to the attention of the Board.

h.Counterparts. This Agreement may be executed in counterparts, each of which shall be deemed an original, but all of which together will constitute one and the same instrument, and facsimile and electronic signatures shall be equivalent to original signatures.

[Signature Page Follows]

IN WITNESS WHEREOF, the parties have executed this Agreement as of the date written below.

By: /s/ Allan Thygesen                

By: /s/ Blake Grayson                

EXHIBIT A

DEFINITIONS

“Cause” will mean the occurrence of one or more of the following:

i.Executive’s willful and continued failure to perform the lawful and reasonable duties and responsibilities of Executive’s position (excluding any failure resulting from Executive’s death or terminal condition, as defined under the Company’s Death or Terminal Condition Policy, as may be amended from time to time) after there has been delivered to Executive a written demand for performance from the Company which describes the basis for the Company’s belief that Executive has not substantially performed Executive’s lawful duties and provides Executive with thirty (30) days to take corrective action, and during which such period reasonable corrective action has not been taken;

ii.any act of personal dishonesty taken by Executive in connection with Executive’s responsibilities as an employee of the Company with the intention or reasonable expectation that such action may result in substantial personal enrichment of Executive;

iii.Executive’s conviction of, or plea of nolo contendere to, a felony;

iv.Executive’s commission of any tortious act, unlawful act or malfeasance which causes or reasonably could cause (for example, if it became publicly known) material harm to the Company’s standing, condition or reputation;

v.any material breach by Executive of the provisions of the At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement or other improper disclosure of the Company’s confidential or proprietary information;

vi.a breach of any fiduciary duty owed to the Company by Executive that has or could reasonably be expected to have a material detrimental effect on the Company’s reputation or business;

vii.Executive (A) obstructing or impeding; (B) endeavoring to influence, obstruct or impede, or (C) failing to materially cooperate with, any investigation authorized by the Board or any governmental or self-regulatory entity (an “Investigation”). However, Executive’s failure to waive attorney-client privilege relating to communications with Executive’s own attorney in connection with an Investigation will not constitute “Cause”; or

viii.A material breach by Executive of any written Company policy or the Company’s written code of conduct that has been made available to Executive prior to such breach;

provided, however, that the action or conduct described in the clauses above (excluding (iii)) will constitute “Cause” only if such action or conduct continues after the Company has provided Executive with written notice thereof and thirty (30) days to cure the same if such action or conduct is curable.

“Change in Control” will have the meaning set forth in the Company’s Amended and Restated 2018 Equity Incentive Plan, excluding subsections (iv) and (v) thereof.

“Change in Control Period” means the period beginning 90 days prior to and ending on the 12- month anniversary of the effective date of a Change in Control.

“COBRA” means the Consolidated Omnibus Budget Reconciliation Act of 1985, as amended together with any analogous provisions of applicable state law.

“Code” means Internal Revenue Code of 1986, as amended, and the Treasury regulations and formal guidance promulgated thereunder, each as may be amended or modified from time to time.

“Good Reason” for Executive’s resignation of employment will exist following the occurrence of any of the following without Executive’s express written consent:

i.a material reduction in Executive’s title, duties or responsibilities without Executive’s consent, including no longer being CFO of a public company;

ii.a material reduction in Executive’s base compensation or annual target incentive bonus, other than a one-time reduction of less than 25% that applies equally to all other senior executives (but subject to the notice, cure period and other requirements set forth below);

iii.any action or inaction that constitutes a material breach by the Company of any material provision of this Agreement or any equity award agreement; or

iv.a relocation of Executive’s principal place of employment to a place that increases Executive’s one-way commute by more than thirty (30) miles as compared to Executive’s then-current principal place of employment immediately prior to such relocation.

In order to resign for Good Reason, Executive must provide written notice to Board within ninety (90) days after the first occurrence of the event giving rise to Good Reason setting forth the basis for Executive’s resignation, allow the Company at least thirty (30) days from receipt of such written notice to cure such event, and if such event is not reasonably cured within such period, Executive must resign from all positions Executive then holds with the Company not later than thirty (30) days after the expiration of the cure period.

The effective date for such a resignation for Good Reason (in the absence of cure) will be the earlier of the following dates: (i) the date of expiration of the Company’s cure period or (ii) the date that the Company advises Executive in writing that it does not intend to cure. For the purposes of delivery of notice under subsection (i) above, a material change or material reduction that occurs incrementally over a period of time (not to exceed twelve (12) months) shall be deemed to have occurred when such change or reduction, in the aggregate, becomes material.

“Qualifying Termination” shall mean the termination of Executive’s employment by the Company without Cause or by Executive with Good Reason.

EXHIBIT B

SECTION 409A AND SECTION 280G MATTERS

It is intended that the Agreement shall comply with the requirements of Section 409A of the Code, and any payments hereunder are intended to be exempt from, or if not so exempt, to comply with the requirements of Section 409A of the Code, and this Agreement shall be interpreted, operated and administered accordingly. To the extent that any provision of the Agreement is ambiguous, but a reasonable interpretation of the provision would cause any payment or benefit to comply with or be exempt from the requirements of Section 409A of the Code, Executive and the Company intend the term to be interpreted as such in order to avoid adverse personal tax consequences under Section 409A.

No severance or other payments or benefits otherwise payable to Executive upon a termination of employment under the Agreement or otherwise will be payable until Executive has a “separation from service” as defined under Treasury Regulation Section 1.409A-l(h), without regard to any alternative definition thereunder.

If the period during which Executive may sign the Release begins in one calendar year and ends in the following calendar year, then no severance payments or benefits that that would constitute deferred compensation within the meaning of Section 409A of the Code will be paid or provided until the later calendar year.

The severance payments and benefits under the Agreement are intended to satisfy the exemptions from application of Section 409A of the Code provided under Treasury Regulations Sections 1.409A- l(b)(4), 1.409A-l(b)(5) and 1.409A-l(b)(9). However, if such exemptions are not available and Executive is a “specified employee” within the meaning of Section 409A of the Code at the time of Executive’s separation from service, then, solely to the extent necessary to avoid adverse personal tax consequences under Section 409A of the Code, any payments payable under the Agreement on account of a separation from service that would constitute deferred compensation within the meaning of Section 409A of the Code and that would (but for this provision) be payable within 6 months following the date of termination, shall instead be paid on the next business day following the expiration of such six month period or, if earlier, upon Executive’s death. Each installment payment under the Agreement is a “separate payment” for purposes of Treasury Regulations Section 1.409A-2(b)(2)(i).

If any payment or benefit (including payments and benefits pursuant to the Agreement) that Executive would receive in connection with a Change in Control from the Company or otherwise (a “Transaction Payment”) would (i) constitute a “parachute payment” within the meaning of Section 280G of the Code, and (ii) but for this sentence, be subject to the excise tax imposed by Section 4999 of the Code (the “Excise Tax”), then the Company shall cause to be determined, before any amounts of the Transaction Payment are paid to Executive, which of the following two alternative forms of payment would result in Executive’s receipt, on an after-tax basis, of the greater amount of Transaction Payments notwithstanding that all or some portion of the Transaction Payment may be subject to the Excise Tax: (1) payment in full of the entire amount of the Transaction Payments (a “Full Payment”), or (2) payment of only a portion of the Transaction Payments so that Executive receives the largest payment possible without the imposition of the Excise Tax (a “Reduced Payment”). For purposes of determining whether to make a Full Payment or a Reduced Payment, the Company shall cause to be taken into account all applicable federal, state, local and foreign income and employment taxes and the Excise Tax (all computed at the highest applicable marginal rate, net of the maximum reduction in federal income taxes which could be obtained from a deduction of such state and local taxes).

If a Reduced Payment is made, (x) Executive shall have no rights to any additional payments and/or benefits constituting the forfeited portion of the Full Payment, and (y) reduction in payments and/or benefits will occur in the manner that results in the greatest economic benefit for Executive. If more than one method of reduction will result in the same economic benefit, the items so reduced will be reduced pro rata. Notwithstanding the foregoing, if such reduction would result in any portion of the Transaction Payments being subject to penalties pursuant to Section 409A that would not otherwise be subject to such penalties, then the reduction method shall be modified so as to avoid the imposition of penalties pursuant to Section 409A as follows: (A) Transaction Payments that are contingent on future events (e.g., being terminated without Cause), shall be reduced (or eliminated) before Transaction Payments that are not contingent on future events; and (B) Transaction Payments that are “deferred compensation” within the meaning of Section 409A shall be reduced (or eliminated) before Transaction Payments that are not deferred compensation within the meaning of Section 409A. In the event that acceleration of vesting of any equity compensation awards is to be reduced, such acceleration of vesting will be cancelled in the reverse order of the date of grant of Executive’s equity awards. In no event will the Company or any stockholder be liable to Executive for any amounts not paid as a result of the operation of this provision.

The professional firm engaged by the Company for general tax purposes as of the day prior to the effective date of the Change in Control shall make all determinations required to be made under this Exhibit B. If the professional firm so engaged by the Company is serving as accountant or auditor for the individual, entity or group effecting the Change in Control, the Company shall appoint a nationally recognized independent registered public accounting firm to make the determinations required hereunder. The Company shall bear all expenses with respect to the determinations by such professional firm required to be made hereunder.

The professional firm engaged to make the determinations hereunder shall provide its calculations, together with detailed supporting documentation, to the Company and Executive within a reasonable period after the date on which Executive’s right to a Transaction Payment is triggered or such other time as reasonably requested by the Company or Executive. If the professional firm determines that no Excise Tax is payable with respect to the Transaction Payment, either before or after the application of the Reduced Amount, it shall furnish the Company and Executive with detailed supporting calculations of its determinations that no Excise Tax will be imposed with respect to such Transaction Payment. Any good faith determinations of the professional firm made hereunder shall be final, binding and conclusive upon the Company and Executive.

Notwithstanding the foregoing, if the Company is privately held as of immediately prior to a Change in Control and it is deemed necessary by the Company to avoid any potential imposition of the adverse tax results provided for by Sections 280G and 4999 of the Code, then as a further condition to any payment or benefit provided for in the Agreement or otherwise, the Company may require Executive to submit any payment or benefit provided for in the Agreement or from any other source that the Company reasonably determines may constitute an “excess parachute payment” (as defined in Section 280G(b)(l) of the Code) for approval by the Company’s stockholders prior to the Closing of the Change in Control in the manner required by the terms of Section 280G(b)(5)(B) of the Code, so that no payments or benefits will be deemed to constitute a “parachute payment” subject to the excise taxes under Sections 280G and 4999 of the Code.

SAN FRANCISCO, CA — May 16, 2023 – DocuSign (NASDAQ:DOCU) today announced the appointment of Blake Grayson as Chief Financial Officer. Blake will succeed Cynthia Gaylor, who as we previously announced will remain as DocuSign’s CFO through the release of the company’s Q1 earnings.

“The leadership team and I are thrilled to partner with Blake to continue to build DocuSign,“ said Allan Thygesen, Chief Executive Officer, DocuSign. “He has exceptional intellect and agility, demonstrated CFO leadership of a high growth, category-leading public software company, and deep operational and finance experience from one of the world’s most innovative companies. Blake will help us unlock both growth and operational efficiency.”

In addition to leading DocuSign’s global finance teams, Blake will focus on ensuring DocuSign delivers against its operating plan, identifying and executing on opportunities for improved monetization and efficiency, and driving the company’s strategic roadmap.

“DocuSign changed the way millions of businesses operate by providing a secure, reliable, and seamless way to manage documents,” said Blake Grayson. “Allan and the rest of the executive team have laid the foundation for growth and have a well-defined strategy in place. I’m looking forward to helping lead the company as it enters its next chapter.”

Most recently, Blake served as the CFO of The Trade Desk leading the company’s overall financial activities, including controllership, tax, treasury, analysis, investor relations, corporate development, facilities, and financial operations. Prior to becoming CFO of The Trade Desk in 2019, Blake served in various finance leadership roles at Amazon for over a decade.

For more information on DocuSign, visit www.docusign.com

About DocuSign DocuSign redefines how the world comes together and agrees, making agreements smarter, easier and more trusted. As part of its industry leading product lineup, DocuSign offers eSignature, the world's #1 way to sign electronically on practically any device, from almost anywhere, at any time. Today, over 1 million customers and more than a billion users in over 180 countries use DocuSign products and solutions to accelerate the process of doing business and simplify people's lives. For more information visit http://www.docusign.com.

Copyright 2023. DocuSign, Inc. is the owner of DOCUSIGN® and all its other marks (www.docusign.com/IP).

Megan Gregorio

media@docusign.com

investors@docusign.com

This press release contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, that are based on our management's beliefs and assumptions, and which statements can involve substantial risk and uncertainties. Forward-looking statements include all statements that are not historical facts and can be identified by terms such as “may,” “will,” “plans,” “potential,” or “continue” or the negative of these words or other similar terms or expressions that concern our expectations, future growth, strategy, plans or intentions. Additional risks and uncertainties affecting our business can be found in our annual report on Form 10-K for the fiscal year ended January 31, 2023 filed on March 27, 2023 with the Securities and Exchange Commission (the “SEC”), and other filings that we make from time to time with the SEC. Any forward-looking statements contained in this press release are based on assumptions that we believe to be reasonable as of this date. Except as required by law, we assume no obligation to update these forward-looking statements, or to update the reasons if actual results differ materially from those anticipated in the forward-looking statements.